ferulic acid hexyl ester | 87024-35-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ferulic acid hexyl ester
• 英文别名: 4-hydroxy-3-methoxy-n-hexyl cinnamate；hexyl ferulate；Hexyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate；hexyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• CAS: 87024-35-9
• 化学式: C₁₆H₂₂O₄
• 分子量: 278.348
• InChiKey: GSUPPTOWPNFMPI-UHFFFAOYSA-N

物化性质

• 沸点：
  404.6±30.0 °C(Predicted)
• 密度：
  1.089±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-正戊氧基苯甲酰氯 、 ferulic acid hexyl ester 在 吡啶 作用下， 生成
  参考文献：
  名称：

  对横向替代和中央桥的介晶依赖

  摘要：

  摘要合成并研究了一种新型酯类同源系列，以了解和确定分子结构对具有常见横向取代的-OCH3 基团和不断变化的端基的液晶特性的影响。小说系列由十二名成员组成。C1至C3成员不是液晶，而其余成员C4至C16是近晶型的，没有表现出向列特征。近晶相的织构为 A 型或 C 型的焦圆锥扇形。近晶中间相的转变温度和织构通过热台偏光显微镜 (POM) 进行观察。过渡曲线（Cr-I 或 Cr-M 和 Sm-I）表现正常。分析和光谱数据支持分子结构。近晶的平均热稳定性为 77。25°C 和 smectogenic 中间相范围从 15°C 到 33°C。本系列的液晶特性与结构相似的同源系列进行了比较。因此，该系列仅具有三个非介晶同系物是近源性的。

  DOI：

  10.1080/15421406.2015.1044637
• 作为产物：
  描述：

  阿魏酸 、 正己醇 在 硫酸 作用下， 以65.3%的产率得到ferulic acid hexyl ester
  参考文献：
  名称：

  对横向替代和中央桥的介晶依赖

  摘要：

  摘要合成并研究了一种新型酯类同源系列，以了解和确定分子结构对具有常见横向取代的-OCH3 基团和不断变化的端基的液晶特性的影响。小说系列由十二名成员组成。C1至C3成员不是液晶，而其余成员C4至C16是近晶型的，没有表现出向列特征。近晶相的织构为 A 型或 C 型的焦圆锥扇形。近晶中间相的转变温度和织构通过热台偏光显微镜 (POM) 进行观察。过渡曲线（Cr-I 或 Cr-M 和 Sm-I）表现正常。分析和光谱数据支持分子结构。近晶的平均热稳定性为 77。25°C 和 smectogenic 中间相范围从 15°C 到 33°C。本系列的液晶特性与结构相似的同源系列进行了比较。因此，该系列仅具有三个非介晶同系物是近源性的。

  DOI：

  10.1080/15421406.2015.1044637

文献信息

• Antiallergic activity of rosmarinic acid esters is modulated by hydrophobicity, and bulkiness of alkyl side chain
  作者：Fengxian Zhu、Zhongming Xu、Lina Yonekura、Ronghua Yang、Hirotoshi Tamura

  DOI：10.1080/09168451.2015.1010478

  日期：2015.7.3

  Methyl, propyl and hexyl esters of rosmarinic, caffeic and p-coumaric acids were tested for antiallergic activity, and rosmarinic acid propyl ester exhibited the greatest β-hexosaminidase release suppression (IC50, 23.7 μM). Quadratic correlations between pIC50 and cLogP (r2 = 0.94, 0.98, and 1.00, respectively) were observed in each acid ester series. The antiallergic activity is modulated by hydrophobicity, and alkyl chain bulkiness.

  摘要 对迷迭香酸、咖啡酸和对香豆酸的甲基、丙基和己基酯进行了抗过敏活性测试，其中迷迭香酸丙基酯表现出最大的β-葡萄糖氨酸酶释放抑制作用（IC50，23.7 μM）。在每个酸酯系列中观察到pIC50和cLogP之间的二次相关性（分别为r2 = 0.94、0.98和1.00）。抗过敏活性受疏水性和烷基链的体积影响。
• Synthesis of Novel Polyphenols Consisted of Ferulic and Gallic Acids, and Their Inhibitory Effects on Phorbol Ester-Induced Epstein–Barr Virus Activation and Superoxide Generation
  作者：Eisaku Nomura、Asao Hosoda、Hideko Morishita、Akira Murakami、Koichi Koshimizu、Hajime Ohigashi、Hisaji Taniguchi

  DOI：10.1016/s0968-0896(01)00361-3

  日期：2002.4

  We prepared novel polyphenols which were esters composed of two naturally occurring products, ferulic and gallic acids, and investigated their inhibitory effects on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced Epstein-Barr virus (EBV) activation and superoxide (O-2(-)) generation. Most of these compounds exhibited significant EBV activation suppression at a concentration of 20 muM and in particular, the ester 5f having 2-metyl-1-butyl group showed high activity. The suppressive effects on O-2(-) generation were also observed in most of the esters. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Alkyl Ferulate Esters as Multifunctional Food Additives: Antibacterial Activity and Mode of Action against <i>Escherichia coli</i> in Vitro
  作者：Yu-gang Shi、Yun-jie Zhu、Shi-yin Shao、Run-run Zhang、Yu Wu、Chen-min Zhu、Xian-rui Liang、Wen-qiang Cai

  DOI：10.1021/acs.jafc.8b04429

  日期：2018.11.14

  This work aims to prepare ferulic acid alkyl esters (FAEs) through the lipase-catalyzed reaction between methyl ferulate and various fatty alcohols in deep eutectic solvents and ascertain their antibacterial activities and mechanisms. Screens of antibacterial effects of FAEs against Escherichia coli ATCC 25922 (E. coli) and Listeria monocytogenes ATCC 19115 (L. monocytogenes) revealed that hexyl ferulate (FAC6) exerted excellent bacteriostatic and bactericidal effects on E. coli and L. monocytogenes (minimum inhibitory concentration (MIC): 1.6 and 0.1 mM, minimum bactericidal concentration (MBC): 25.6 and 0.2 mM, respectively). The antibacterial mechanism of FAC6 against E. coli was systematically studied to facilitate its practical use as a food additive with multifunctionalities. The growth and time-kill curves implied the partial cell lysis and inhibition of the growth of E. coli caused by FAC6. The result related to propidium iodide uptake and cell constituents' leakage (K+, proteins, nucleotides, and beta-galactosidase) implied that bacterial cytomembranes were substantially compromised by FAC6. Variations on morphology and cardiolipin microdomains and membrane hyperpolarization of cells visually verified that FAC6 induced cell elongation and destructed the cell membrane with cell wall perforation. SDS-PAGE analysis and alterations of fluorescence spectra of bacterial membrane proteins manifested that FAC6 caused significant changes in constitutions and conformation of membrane proteins. Furthermore, it also could bind to minor grooves of E. coli DNA to form complexes. Meanwhile, FAC6 exhibited antibiofilm formation activity. These findings indicated that that FAC6 has promising potential to be developed as a multifunctional food additive.
• Mesomorphism dependence on lateral substitution and central bridge
  作者：M. S. Vadodaria、K. D. Ladva、A. V. Doshi、J. J. Travadi

  DOI：10.1080/15421406.2015.1044637

  日期：2016.1.2

  transition temperatures and textures of smectic mesophases were observed through hot stage polarizing microscopy (POM). The transition curves (Cr-I or Cr-M and Sm-I) behaved in normal manner. Analytical and spectral data support the molecular structures. Average thermal stability for smectic is 77.25°C and smectogenic mesophase ranges from 15°C to 33°C. Liquid crystal properties of the present series are

  摘要合成并研究了一种新型酯类同源系列，以了解和确定分子结构对具有常见横向取代的-OCH3 基团和不断变化的端基的液晶特性的影响。小说系列由十二名成员组成。C1至C3成员不是液晶，而其余成员C4至C16是近晶型的，没有表现出向列特征。近晶相的织构为 A 型或 C 型的焦圆锥扇形。近晶中间相的转变温度和织构通过热台偏光显微镜 (POM) 进行观察。过渡曲线（Cr-I 或 Cr-M 和 Sm-I）表现正常。分析和光谱数据支持分子结构。近晶的平均热稳定性为 77。25°C 和 smectogenic 中间相范围从 15°C 到 33°C。本系列的液晶特性与结构相似的同源系列进行了比较。因此，该系列仅具有三个非介晶同系物是近源性的。